Arachidonoyl Glycine-d8

Arachidonoyl Glycine-d₈

Cayman Chemical Item Number 10007531

N-Arachidonyl Glycine-d₈; NAGly-d₈

Description

Arachidonoyl glycine-d₈ (NAGly-d₈) contains eight deuterium atoms at the 5, 6, 8, 9, 11, 12, 14, and 15 positions. It is intended for use as an internal standard for the quantification of NAGly by GC- or LC-mass spectrometry. NAGly has been isolated from cell cultures treated with arachidonoyl ethanolamide (AEA),¹ from extracts of mammalian brain,^2,3 and has also been synthesized as an analog of AEA for structure/activity testing.⁴ NAGly may be produced endogenously via oxidation of AEA, or by transacylation of arachidonoyl coenzyme A. NAGly is reported to have analgesic activities in whole animal experiments.^1,2,3 Since it seems to be a very poor ligand for the CB₁ receptor,⁴ these effects are probably mediated via other signalling pathways.

1 Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat 61 29-41 (2000).

2 Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification and characterization of an endogenous anandamide-like compound: N-arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids 78 (2001).

3 Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276(46) 42639-42644 (2001).

4 Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 659-667 (1997).

Synonyms

N-Arachidonyl Glycine-d8
NAGly-d8

Formal Name

N-[1-oxo-5Z,8Z,11Z,14Z-eicosatetraenyl]-glycine,5,6,8,9,11,12,14,15-d8

Molecular Formula

C₂₂H₂₇D₈NO₃

Formula Weight

369.6

Formulation

A solution in ethanol

Purity

≥99% deuterated forms (d1-d8)

Stability

1 year

Storage

-20°C

Shipping

Wet ice in continental US; may vary elsewhere

SMILES

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CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCC(=O)O

Background Reading

Burstein, S.H., Rossetti, R.G., Yagen, B., et al. Oxidative metabolism of anandamide. Prostaglandins Other Lipid Mediat 61 29-41 (2000).

Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification and characterization of an endogenous anandamide-like compound: N-arachidonylglycine (NAGly). ICRS 2001 Symposium on the Cannabinoids 78 (2001).

Huang, S.M., Bisogno, T., Petros, T.J., et al. Identification of a new class of molecules, the arachidonyl amino acids, and characterization of one member that inhibits pain. J Biol Chem 276(46) 42639-42644 (2001).

Sheskin, T., Hanus, L., Slager, J., et al. Structural requirements for binding of anandamide-type compounds to the brain cannabinoid receptor. J Med Chem 40 659-667 (1997).

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Arachidonoyl Glycine-d₈